Principal IT Project Manager

The Wisconsin Foundation and Alumni Association is a nonprofit organization supporting UW-Madison through fundraising, alumni relations, and engagement. The Principal IT Project Manager will lead complex IT projects while owning and advancing the organization’s project management methodology, governance standards, tooling strategy, and continuous improvement practices. The role also mentors project managers, advises senior leadership, and promotes AI-assisted tools to improve project delivery.

Responsibilities:

• Define, own, and maintain the organization’s project management methodology, selecting and tailoring frameworks (Agile, Waterfall, Hybrid, Kanban) to organizational context and project type
• Establish and enforce PMO governance processes including project intake, stage-gate reviews, and escalation paths
• Develop, publish, and maintain a comprehensive library of PM standards, templates, playbooks, and toolkits (charters, RAID logs, status reports, lessons learned, etc.)
• Define and operationalize project classification tiers (e.g., small/medium/large/transformational) with associated methodology and oversight requirements
• Lead periodic PMO maturity assessments and develop roadmaps to advance organizational project management capability
• Establish metrics and KPIs for project performance and PMO effectiveness; report findings to senior leadership
• Serve as a mentor and go-to resource for project managers at all levels, providing guidance on methodology application, PM standards, and stakeholder management
• Develop PM competency frameworks and reference materials that support consistent standards adoption across the team
• Stay current with industry trends (PMI, Agile Alliance, Gartner) and proactively recommend methodology updates
• Manage a portfolio of complex, high-visibility IT projects from initiation through closure, ensuring delivery on time, within scope, and within budget
• Collaborate with senior leadership and stakeholders to define project objectives, gather requirements, and align projects to strategic business goals
• Lead cross-functional project teams through design, development, testing, and implementation phases
• Identify, assess, and actively manage risks, issues, dependencies, and change requests across all assigned projects
• Maintain comprehensive project documentation and deliver clear, concise status communications to stakeholders at all levels
• Flex into Product Owner, Scrum Master, or Business Analyst roles as project needs require
• Own the selection, configuration, and adoption strategy for PMO tooling (Jira, Workfront, MS Project, Power BI dashboards, etc.)
• Develop standardized reporting frameworks and portfolio dashboards for executive and operational audiences
• Actively identify opportunities to apply AI tools and AI-assisted PMO tooling capabilities to automate the production and distribution of PM artifacts, reduce administrative burden, and enhance project delivery through intelligent scheduling, risk flagging, resource forecasting, and stakeholder communication — incorporating proven approaches into PMO standards
• Lead lessons-learned programs and translate insights into actionable process improvements embedded in PMO standards
• Champion a culture of continuous improvement, data-driven decision-making, and delivery excellence across the project management community
• Build and sustain trusted relationships with IT leadership, business unit leaders, and executive sponsors
• Serve as a key advisor to leadership on project delivery risks, resource capacity, and methodology effectiveness
• Communicate complex project and portfolio information clearly to both technical and non-technical audiences

Requirements:

• Bachelor's degree in Information Technology, Project Management, Business Administration, or equivalent experience
• 10 + years of progressive IT project management experience, with at least 3 + years in a lead, principal, or PMO-level capacity
• Demonstrated experience building or maturing a PMO or PM practice, including methodology design and standards implementation
• Proven track record delivering complex, enterprise-scale IT projects with measurable business impact
• Expert-level command of multiple project management methodologies: Agile, Scrum, Kanban, SAFe, Waterfall, and Hybrid approaches
• Proficiency in PMO tooling including Jira, Workfront, MS Project, Microsoft Teams, SharePoint, and portfolio/reporting dashboards
• Strong understanding of SDLC, IT infrastructure, and enterprise systems (CRM, ERP, Financial Reporting platforms preferred)
• Experience developing PM standards, templates, playbooks, and governance frameworks
• Exceptional leadership, influence, and facilitation skills; able to drive alignment across diverse, cross-functional stakeholders without direct authority
• Strong coaching and mentoring capabilities with a focus on elevating peers' application of PM methodology and standards
• Excellent written and verbal communication skills, including executive-level presentation and reporting
• High analytical aptitude; able to synthesize data and translate insights into strategic recommendations. Comfortable managing ambiguity, competing priorities, and organizational change
• Remote candidates must reside in the following states to be considered: Arizona, Colorado, Illinois, Iowa, Kentucky, Minnesota, Nebraska, New Mexico, New York, Texas, and Wisconsin
• PMP certification and experience building or maturing a PM practice are strongly preferred
• Project Management: PMP (Project Management Professional), PRINCE2 Practitioner, PMI-PBA (Business Analysis)
• Agile & Delivery**: CSM / A-CSM (Scrum Master), PMI-ACP (Agile Certified Practitioner), SAFe Program Consultant (SPC)